Gary Gershoff/WireImage(LOS ANGELES) -- Ashlee Simpson has been spotted out holding hands with the son of a music icon.

The “Pieces of Me” singer went out with Evan Ross, son of legendary singer Diana Ross, on not just one, but two occasions in less than 24 hours.

Simpson, 28, and Ross, 24, first hung out Monday night at the Roosevelt Hotel, staying until 1:30 a.m. At the end of their night, Ross led way out of the hotel’s club Teddy’s, guiding her with his right hand, while casually enjoying a smoke in his left.

The next afternoon, the two were spotted together again in West Hollywood, grabbing lunch. Ross wore what appeared to be the same pair of knee-patched jeans he had on the night before while the single mother to son Bronx, 4, had changed into dark jeans and a relaxed white top.

Previously Simpson was married to Pete Wentz, 33, for three years until they divorced in 2011. Later that year, she began dating Boardwalk Empire actor Vincent Piazza until their breakup late last year.